Cupressuflavone
Basic information
- CAS
3952-18-9- Standard SMILES
O=c1cc(-c2ccc(O)cc2)oc2c(-c3c(O)cc(O)c4c(=O)cc(-c5ccc(O)cc5)oc34)c(O)cc(O)c12- InChIKey
LADPNODMUXOPRG-UHFFFAOYSA-N- Molecular formula
- C30H18O10
- Average molar mass
- 538.5 g/mol
- Monoisotopic mass
- 538.08999677
Overview
Cupressuflavone is a biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-8 of the two chromene rings respectively. Isolated from Cupressus sempervirens and Juniperus occidentalis, it exhibits free radical scavenging and antielastase activities. It has a role as a metabolite, a radical scavenger and an EC 3.4.21.37 (leukocyte elastase) inhibitor. It is a hydroxyflavone, a ring assembly and a biflavonoid.
Names & identifiers
- Preferred name
- Cupressuflavone
- IUPAC
- 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
- English name
- CUPRESSUFLAVONE TRIHYDRATE
- Molecular formula
- C30H18O10
- Molecular weight
- 538.46
Names & synonyms
Cupressuflavone3952-18-98,8''-BiapigeninCHEBI:39608-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-oneDTXSID804151538-(5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-oneRefChem:128816DTXCID70366004CUPRESSUFLAVONE TRIHYDRATEMFCD00210489MLS002472961
Show more names
8,8''-BiapigeninylCUPRESSUFLAVONE WITH HPLCCupressuflavone 3-hydrateCUPRESSUFLAVONE Trihydrate hplcCUPRESSUFLAVONE TRIHYDRATE WITH HPLC4',4''',5,5'',7,7''-HEXAHYDROXY-8,8''-BIFLAVONE5,5',7,7'-Tetrahydroxy-2,2'-bis(4-hydroxyphenyl)[8,8'-bi(4H-1-benzopyran)]-4,4'-dione[8,8'-Bi-4H-1-benzopyran]-4,4'-dione, 5,5',7,7'-tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-
CHEMBL1208973SMR001397068SCHEMBL505213orb1682876SCHEMBL31670258HMS2271A07HY-N9173BDBM50323213
Properties
Computed structural properties
- XLogP
- 5
- Topological polar surface area
- 174 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 3
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 957
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Biflavonoids and polyflavonoids [PK1204]
Physicochemical properties
- Melting point
- 400 °C · >400°C
- Boiling point
- 927 · 927.0±65.0 °C(Predicted)
- Density
- 1.656 · 1.656±0.06 g/cm3(Predicted)
- pka
- 5.43 · 5.43±0.40(Predicted)
- form
- Solid
- color
- Light yellow to yellow
- LogP
- 3.07 · 3.070 (est)
Chemistry & industry
Applications
UsesCupressuflavone is a natural product that can be found in Cupressus macrocarpa. Cupressuflavone exhibits anti-inflammatory and antiulcerogenic activities. Cupressuflavone also show protective effects against CCl4-induced hepato- and nephrotoxicity in mice[1][2][3].
Additional notes
DefinitionChEBI: A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-8 of the two chromene rings respectively. Isolated from Cupressus sempervirens and Juniperus occidentalis, i exhibits free radical scavenging and antielastase activities.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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